SCOPUS 정보 검색 플랫폼 - 논문 보기

메뉴 건너뛰기

Tetrahedron Letters

Volumn 54, Issue 8, 2013, Pages 1029-1031

A hydrozirconation/iodination-mediated access to tetrahydroquinolizinium salts. Application to the synthesis of Lupinine and (-)-Epiquinamide

(5) Hajri, Majdi a Blondelle, Clément a Martinez, Agathe a Vasse, Jean Luc a Szymoniak, Jan a

a UNIVERSITÉ DE REIMS CHAMPAGNE ARDENNE (France)

Author keywords

( ) Epiquinamide; Alkaloids; Hydrozirconation; Lupinine; Tetrahydroquinolizinium salts

Indexed keywords

ALKENE DERIVATIVE; EPIQUINAMIDE; LUPININE; QUINOLIZINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; HYDROGENATION; IODINATION; SUBSTITUTION REACTION;

EID: 84872283226 PISSN: 00404039 EISSN: 18733581 Source Type: Journal
DOI: 10.1016/j.tetlet.2012.12.073 Document Type: Article

Times cited : (16)

References (47)

1
- 34247109045
- D.J. Newman, and G.M. Cragg J. Nat. Prod. 70 2007 461 477
- (2007) J. Nat. Prod. , vol.70 , pp. 461-477
- Newman, D.J.¹ Cragg, G.M.²

2
- 23944472732
- J.W. Daly Cell. Mol. Neurobiol. 25 2005 513 5523
- (2005) Cell. Mol. Neurobiol. , vol.25 , pp. 513-5523
- Daly, J.W.¹

3
- 0031931850
- J.W. Daly J. Nat. Prod. 61 1998 162 172
- (1998) J. Nat. Prod. , vol.61 , pp. 162-172
- Daly, J.W.¹

4
- 34548859532
- N. Toyooka, S. Kobayashi, D. Zhou, H. Tsuneki, T. Wada, H. Sakai, H. Nemoto, T. Sasaoka, H.M. Garraffo, T.F. Spande, and J.W. Daly Bioorg. Med. Chem. Lett. 17 2007 5872 5875
- (2007) Bioorg. Med. Chem. Lett. , vol.17 , pp. 5872-5875
- Toyooka, N.¹ Kobayashi, S.² Zhou, D.³ Tsuneki, H.⁴ Wada, T.⁵ Sakai, H.⁶ Nemoto, H.⁷ Sasaoka, T.⁸ Garraffo, H.M.⁹ Spande, T.F.¹⁰ Daly, J.W.¹¹

5
- 55949132372
- M.A. Wijdeven, R. Wijtmans, R.J. van den Berg, W. Noorduin, H.E. Schoemaker, T. Sonke, F.L. van Delft, R.H. Blaauw, R.W. Fitch, T.F. Spande, J.W. Daly, and F.P. Rutjes Org. Lett. 10 2008 4001 4003
- (2008) Org. Lett. , vol.10 , pp. 4001-4003
- Wijdeven, M.A.¹ Wijtmans, R.² Van Den Berg, R.J.³ Noorduin, W.⁴ Schoemaker, H.E.⁵ Sonke, T.⁶ Van Delft, F.L.⁷ Blaauw, R.H.⁸ Fitch, R.W.⁹ Spande, T.F.¹⁰ Daly, J.W.¹¹ Rutjes, F.P.¹²

6
- 33645899298
- P.Q. Huang, Z.Q. Guo, and Y.P. Ruan Org. Lett. 8 2006 1435 1438
- (2006) Org. Lett. , vol.8 , pp. 1435-1438
- Huang, P.Q.¹ Guo, Z.Q.² Ruan, Y.P.³

7
- 77949778574
- G. Cheng, X. Wang, D. Su, H. Liu, F. Liu, and Y. Hu J. Org. Chem. 75 2010 1911 1916
- (2010) J. Org. Chem. , vol.75 , pp. 1911-1916
- Cheng, G.¹ Wang, X.² Su, D.³ Liu, H.⁴ Liu, F.⁵ Hu, Y.⁶

8
- 4644290053
- B.-F. Chen, M.-R. Tasi, C.-Y. Yang, J.-K. Chang, and N.-C. Chang Tetrahedron 60 2004 10223 10231
- (2004) Tetrahedron , vol.60 , pp. 10223-10231
- Chen, B.-F.¹ Tasi, M.-R.² Yang, C.-Y.³ Chang, J.-K.⁴ Chang, N.-C.⁵

9
- 47049116957
- Y. Nishikawa, M. Kitajima, and H. Takayama Org. Lett. 10 2008 1987 1990
- (2008) Org. Lett. , vol.10 , pp. 1987-1990
- Nishikawa, Y.¹ Kitajima, M.² Takayama, H.³

10
- 84855540058
- I. Bosque, J.C. González-Gómez, F. Foubelo, and M. Yus J. Org. Chem. 77 2012 780 784
- (2012) J. Org. Chem. , vol.77 , pp. 780-784
- Bosque, I.¹ González-Gómez, J.C.² Foubelo, F.³ Yus, M.⁴

11
- 78449255211
- M. Fellah, M. Santarem, G. Lhommet, and V. Mouriès-Mansuy J. Org. Chem. 75 2010 7803 7808
- (2010) J. Org. Chem. , vol.75 , pp. 7803-7808
- Fellah, M.¹ Santarem, M.² Lhommet, G.³ Mouriès-Mansuy, V.⁴

12
- 78650355298
- E. Airiau, N. Girard, M. Pizzeti, J. Salvadori, M. Taddei, and A. Mann J. Org. Chem. 75 2010 8670 8673
- (2010) J. Org. Chem. , vol.75 , pp. 8670-8673
- Airiau, E.¹ Girard, N.² Pizzeti, M.³ Salvadori, J.⁴ Taddei, M.⁵ Mann, A.⁶

13
- 0034627339
- M.G.M. D'Oca, R.A. Pilli, and I. Vencato Tetrahedron Lett. 41 2000 9709 9712
- (2000) Tetrahedron Lett. , vol.41 , pp. 9709-9712
- D'Oca, M.G.M.¹ Pilli, R.A.² Vencato, I.³

14
- 36348949660
- A. Voituriez, F. Ferreira, A. Pérez-Luna, and F. Chemla Org. Lett. 9 2007 4705 4708
- (2007) Org. Lett. , vol.9 , pp. 4705-4708
- Voituriez, A.¹ Ferreira, F.² Pérez-Luna, A.³ Chemla, F.⁴

15
- 78650519680
- L.S. Santos, Y. Mirabal-Gallardo, N. Shankaraiah, and M.J. Simirgiotis Synthesis 2011 51 56
- (2011) Synthesis , pp. 51-56
- Santos, L.S.¹ Mirabal-Gallardo, Y.² Shankaraiah, N.³ Simirgiotis, M.J.⁴

16
- 0026040945
- P.S. Liu, R.S. Rogers, M.S. Kang, and P.S. Sunkara Tetrahedron Lett. 32 1991 5853 5856
- (1991) Tetrahedron Lett. , vol.32 , pp. 5853-5856
- Liu, P.S.¹ Rogers, R.S.² Kang, M.S.³ Sunkara, P.S.⁴

17
- 48849106068
- M. Ahari, A. Perez, C. Menant, J.-L. Vasse, and J. Szymoniak Org. Lett. 10 2008 2473 2476
- (2008) Org. Lett. , vol.10 , pp. 2473-2476
- Ahari, M.¹ Perez, A.² Menant, C.³ Vasse, J.-L.⁴ Szymoniak, J.⁵

18
- 0000740010
- Y.C. Hwang, W. Frank, and F.W. Fowler J. Org. Chem. 50 1985 2719 2726
- (1985) J. Org. Chem. , vol.50 , pp. 2719-2726
- Hwang, Y.C.¹ Frank, W.² Fowler, F.W.³

19
- 0037198756
- J. Barluenga, C. Mateos, F. Aznar, and C. Carlos Valdés Org. Lett. 4 2002 1971 1974
- (2002) Org. Lett. , vol.4 , pp. 1971-1974
- Barluenga, J.¹ Mateos, C.² Aznar, F.³ Carlos Valdés, C.⁴

20
- 67650551471
- L. Cui, Y. Peng, and L. Zhang J. Am. Chem. Soc. 131 2009 8394 8395
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 8394-8395
- Cui, L.¹ Peng, Y.² Zhang, L.³

21
- 77956226520
- T. Tite, F. Jacquelin, L. Bischoff, C. Fruit, and F. Marsais Tetrahedron: Asymmetry 21 2010 2032 2036
- (2010) Tetrahedron: Asymmetry , vol.21 , pp. 2032-2036
- Tite, T.¹ Jacquelin, F.² Bischoff, L.³ Fruit, C.⁴ Marsais, F.⁵

22
- 38849126849
- R. Azzouz, C. Fruit, L. Bischoff, and F. Marsais J. Org. Chem. 73 2008 1154 1157
- (2008) J. Org. Chem. , vol.73 , pp. 1154-1157
- Azzouz, R.¹ Fruit, C.² Bischoff, L.³ Marsais, F.⁴

23
- 38349087291
- M. Ahari, A. Joosten, J.-L. Vasse, and J. Szymoniak Synthesis 2008 61 68
- (2008) Synthesis , pp. 61-68
- Ahari, M.¹ Joosten, A.² Vasse, J.-L.³ Szymoniak, J.⁴

24
- 77953277214
- P.-O. Delaye, T.K. Pradhan, E. Lambert, J.-L. Vasse, and J. Szymoniak Eur. J. Org. Chem. 2010 3395 3406
- (2010) Eur. J. Org. Chem. , pp. 3395-3406
- Delaye, P.-O.¹ Pradhan, T.K.² Lambert, E.³ Vasse, J.-L.⁴ Szymoniak, J.⁵

25
- 0142091145
- J.P. Michael Nat. Prod. Rep. 20 2003 458 475
- (2003) Nat. Prod. Rep. , vol.20 , pp. 458-475
- Michael, J.P.¹

26
- 38849102334
- J.P. Michael Nat. Prod. Rep. 25 2008 139 165
- (2008) Nat. Prod. Rep. , vol.25 , pp. 139-165
- Michael, J.P.¹

27
- 0142156733
- R.W. Fitch, H.M. Garraffo, T.F. Spande, H.J. Yeh, and J.W. Daly J. Nat. Prod. 66 2003 1345 1350
- (2003) J. Nat. Prod. , vol.66 , pp. 1345-1350
- Fitch, R.W.¹ Garraffo, H.M.² Spande, T.F.³ Yeh, H.J.⁴ Daly, J.W.⁵

28
- 33750586143
- Compound 1 was prepared according to
- Compound 1 was prepared according to: A.K. Katritzky, K.R. Idzik, A.A.A. Abdel-Fattah, J. Soloducho, and P.J. Steel Synthesis 2006 3377 3388
- (2006) Synthesis , pp. 3377-3388
- Katritzky, A.K.¹ Idzik, K.R.² Abdel-Fattah, A.A.A.³ Soloducho, J.⁴ Steel, P.J.⁵

29
- 75749146979
- For recent synthesis of optically active Lupinine, see: E. Airiau, T. Spangenberg, N. Girard, B. Breit, and A. Mann Org. Lett. 12 2010 528 531
- (2010) Org. Lett. , vol.12 , pp. 528-531
- Airiau, E.¹ Spangenberg, T.² Girard, N.³ Breit, B.⁴ Mann, A.⁵

30
- 80051795519
- S. Fustero, J. Moscardó, M. Sánchez-Roselló, S. Flores, M. Guerola, and C. del Pozo Tetrahedron 67 2011 7412 7417
- (2011) Tetrahedron , vol.67 , pp. 7412-7417
- Fustero, S.¹ Moscardó, J.² Sánchez-Roselló, M.³ Flores, S.⁴ Guerola, M.⁵ Del Pozo, C.⁶

31
- 84887246958
- L. Silva Santos, Y. Mirabal-Gallardo, N. Shankaraiah, and M.J. Simirgiotis Synthesis 2011 51 56
- (2011) Synthesis , pp. 51-56
- Silva Santos, L.¹ Mirabal-Gallardo, Y.² Shankaraiah, N.³ Simirgiotis, M.J.⁴

32
- 46649090552
- R. Noël, M.-C. Fargeau-Bellassoued, C. Vanucci-Bacqué, and G. Lhommet Synthesis 2008 1948 1954
- (2008) Synthesis , pp. 1948-1954
- Noël, R.¹ Fargeau-Bellassoued, M.-C.² Vanucci-Bacqué, C.³ Lhommet, G.⁴

33
- 3142683132
- S. Ma, and B. Ni Chem. Eur. J. 10 2004 3286 3300
- (2004) Chem. Eur. J. , vol.10 , pp. 3286-3300
- Ma, S.¹ Ni, B.²

34
- 2542457448
- C. Agami, L. Dechoux, S. Hebbe, and C. Ménard Tetrahedron 60 2004 5433 5438
- (2004) Tetrahedron , vol.60 , pp. 5433-5438
- Agami, C.¹ Dechoux, L.² Hebbe, S.³ Ménard, C.⁴

35
- 58849121764
- For recent syntheses of Epiquinamide see: S. Gosh, and J. Shashidhar Tetrahedron Lett. 50 2009 1177 1179
- (2009) Tetrahedron Lett. , vol.50 , pp. 1177-1179
- Gosh, S.¹ Shashidhar, J.²

36
- 33750036130
- T.L. Suyama, and W.H. Gerwick Org. Lett. 8 2006 4541 4543
- (2006) Org. Lett. , vol.8 , pp. 4541-4543
- Suyama, T.L.¹ Gerwick, W.H.²

37
- 24944525408
- M.A. Wijdeven, P.N.M. Botman, R. Wijtmans, H.E. Schoemaker, F.P.J.T. Rutjes, and R.H. Blaauw Org. Lett. 7 2005 4005 4007
- (2005) Org. Lett. , vol.7 , pp. 4005-4007
- Wijdeven, M.A.¹ Botman, P.N.M.² Wijtmans, R.³ Schoemaker, H.E.⁴ Rutjes, F.P.J.T.⁵ Blaauw, R.H.⁶

38
- 33645899298
- P.-Q. Huang, Z.-Q. Guo, and Y.-P. Ruan Org. Lett. 8 2006 1435 1438
- (2006) Org. Lett. , vol.8 , pp. 1435-1438
- Huang, P.-Q.¹ Guo, Z.-Q.² Ruan, Y.-P.³

39
- 33744990855
- S.T. Tong, and D. Barker Tetrahedron Lett. 47 2006 5017 5020
- (2006) Tetrahedron Lett. , vol.47 , pp. 5017-5020
- Tong, S.T.¹ Barker, D.²

40
- 66149142252
- A.K. Srivastana, S.K. Das, and G. Panda Tetrahedron 65 2009 5322 5327
- (2009) Tetrahedron , vol.65 , pp. 5322-5327
- Srivastana, A.K.¹ Das, S.K.² Panda, G.³

41
- 17744395123
- T. Vilaivan, C. Winotapan, V. Banphavichit, T. Shinada, and Y. Ohfune J. Org. Chem. 70 2005 3464 3471
- (2005) J. Org. Chem. , vol.70 , pp. 3464-3471
- Vilaivan, T.¹ Winotapan, C.² Banphavichit, V.³ Shinada, T.⁴ Ohfune, Y.⁵

42
- 78649328344
- P.-O. Delaye, M. Ahari, J.-L. Vasse, and J. Szymoniak Tetrahedron: Asymmetry 21 2010 2505 2511
- (2010) Tetrahedron: Asymmetry , vol.21 , pp. 2505-2511
- Delaye, P.-O.¹ Ahari, M.² Vasse, J.-L.³ Szymoniak, J.⁴

43
- 79953165400
- T.K. Pradhan, S. Khrishnan, J.-L. Vasse, and J. Szymoniak Org. Lett. 13 2011 1793 1795
- (2011) Org. Lett. , vol.13 , pp. 1793-1795
- Pradhan, T.K.¹ Khrishnan, S.² Vasse, J.-L.³ Szymoniak, J.⁴

44
- 62649136562
- R.W. Fitch, G.D. Sturgeon, S.R. Patel, T.F. Spande, H.M. Garraffo, J.W. Daly, and R.H. Blaauw J. Nat. Prod. 72 2009 243 247
- (2009) J. Nat. Prod. , vol.72 , pp. 243-247
- Fitch, R.W.¹ Sturgeon, G.D.² Patel, S.R.³ Spande, T.F.⁴ Garraffo, H.M.⁵ Daly, J.W.⁶ Blaauw, R.H.⁷

45
- 73149105739
- S. Chandrasekhar, M. Bodugam, and K. Mitta J. Org. Chem. 74 2009 9531 9534
- (2009) J. Org. Chem. , vol.74 , pp. 9531-9534
- Chandrasekhar, S.¹ Bodugam, M.² Mitta, K.³

46
- 0040846103
- T. Miyadera, and Y. Kishida Tetrahedron 25 1969 209
- (1969) Tetrahedron , vol.25 , pp. 209
- Miyadera, T.¹ Kishida, Y.²

47
- 74949099493
- M. Valpuesta, M. Ariza, A. Diaz, G. Torres, and R. Suau Eur. J. Org. Chem. 2010 638 645
- (2010) Eur. J. Org. Chem. , pp. 638-645
- Valpuesta, M.¹ Ariza, M.² Diaz, A.³ Torres, G.⁴ Suau, R.⁵

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.